Bulletin of the Korean Chemical Society

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Friedel-Crafts Type alkylation of 1,2,3,4,5,6,7,8,-Octahydroanthracene with Vinylchlorosilanes:Synthesis of Mono,Bis[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8,-Octahydroanthracenes

  • Published : 2002.09.20
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Abstract

Friedel-Crafts alkylation reaction of an isomeric mixture of 1,2,3,4,5,6,7,8- (2) and 1,2,3,4,5,6,7,8-octahydrophenanthrene (2') with excess vinylchlorosilanes such as vinyl(methyl)dichlorosilane (1a) and vinyltrichlorosilane (1b) in the presence of aluminum chloride catalyst at 80 $^{\circ}C$ gives only one dialkylated products, 9,10-bis[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydroanthrenes [(Cl2XSiCH2CH2)2C14H16: X = Me (4a), Cl (4b)] in good yields, but 9,10-bis[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydrophenanthrenes are not obtained. However, monoalkylation of 2 with 1 affords a mixture of both isomeric compounds, 9-[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydroanthracenes 3 and -phenanthrenes 3'. The yield of product 3' is always higher than that of 3. When a mixture of 3 and 3' is alkylated again with 1, only product 4 without phenanthrene type compounds is obtained, indicating that the isomerizations between 2 and 2', or 3 and 3'occur under the alkylation condition. The alkylation with dimethylvinylchlorosilane or trimethylvinylsilane did not proceed. The structure of 4a is determined by X-ray single crystal diffraction analysis.

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References

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Cited by

  1. Friedel—Crafts Type Alkylation of 1,2,3,4,5,6,7,8-Octahydroanthracene with Vinylchlorosilanes: Synthesis of Mono, Bis[2-(chlorosilyl)ethyl]1,2,3,4,5,6,7,8-octahydroanthracenes. vol.34, pp.9, 2002, https://doi.org/10.1002/chin.200309168